1-chloro-2,3,3-trifluoropropene (CHCl═CF—CHF2. HCFO-1233 yd. hereinafter, also mentioned as 1233 yd.) is a compound which is substituted for 3,3-dichloro-1,1,1,2,2-pentafluoropropane (CF3—CF2—CHCl2, HCFC-225ca) and 1,3-dichloro-1,1,2,2,3-pentafluoropropane (CClF2—CF2—CClFH, HCFC-225cb) and used for new cleaning agent, refrigerant, foaming agent, solvent, and aerosol applications which have a small global warming potential (GWP).
In this description, regarding halogenated hydrocarbon, an abbreviated name of the compound is mentioned in parentheses behind a compound name, and the abbreviated name is used instead of the compound name as necessary in this description.
In 1233 yd, a Z-isomer and an E-isomer which are geometric isomers exist according to positions of substituents on a double bond. When the compound name or the abbreviated name of the compound is used unless otherwise stated in this description, at least one type selected from the Z-isomer and the E-isomer is indicated, and when (E) or (Z) is denoted behind the compound name or the abbreviated name of the compound, an (E)-isomer or a (Z)-isomer of each compound is indicated. For example, HCFO-1233 yd(Z) indicates the Z-isomer, and HCFO-1233 yd(E) indicates the E-isomer.
As a manufacturing example of 1233 yd, an example in Patent Reference 1 (International Publication WO 1994/14737) mentions that when 3-chloro-1,1,2,2-tetrafluoropropane (CHF2—CF2—CH2Cl. HCFC-244 ca. hereinafter, also mentioned as 244 ca.) and hydrogen fluoride are each introduced in a gas state under a nitrogen gas stream into a reaction tube made of HASTELLOY C and filled with a chromium hydroxide catalyst, a small amount of 1233 yd is by-produced with 1,1,2,2,3-pentafluoropropane (CHF2—CF2—CH2F, HCFC-245ca).
However, the reaction mentioned in Patent Reference 1 is not suitable for mass production on an industrial scale because a conversion ratio of the raw materials is about 70%, and a production amount of 1233 yd is a by-production amount and a very small amount.
The present inventors have considered a de-HX reaction (where, X in formulas indicates Cl, I, or Br) in which a compound represented by the following formula (A) or a compound represented by the following formula (B) is used as a raw material, as another possibility of manufacturing 1233 yd.

However, either of these compounds is not an easily obtainable compound, and there is not a method of industrially easily manufacturing them either, so that they are difficult to obtain. In addition, in a compound (CHF2—CHF—CHFCl, HCFC-244ea) in which X is F in the formula (B), a dehydrochlorination reaction has priority over the de-HX reaction, and therefore 1233 yd cannot be selectively obtained.